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Upcoming Chicago Events

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Al Jackson at The Comedy Bar
Jun21
Music & Comedy

Al Jackson at The Comedy Bar

Al Jackson is a Los Angeles-based stand-up comedian, writer, and TV/radio personality best known for his special “Comedy Central Presents: Al Jackson” and for his role…

Saturday, June 21st
7:30 p.m.9:00 p.m.
The Comedy Bar
500 N. LaSalle St.
ComedySportz Chicago
Jun21
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Saturday, June 21st
8:00 p.m.9:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Ryan Adams: Heartbreaker ’25 World Tour
Jun21
Music & Comedy

Ryan Adams: Heartbreaker ’25 World Tour

Singer-songwriter Ryan Adams will perform live at The Chicago Theatre on June 21, 2025.

Saturday, June 21st
8:00 p.m.11:00 p.m.
The Chicago Theatre
175 N. State
Here 4 A Bit *Naughty Improv
Jun21
Music & Comedy, Theatre & Performing Arts

Here 4 A Bit *Naughty Improv

Join us again for a whose line styled night of explosive laughter that will titillate your “funny” bone. Fast paced short form improv, hilarious songs,…

Saturday, June 21st
9:00 p.m.10:00 p.m.
The Second City
1616 N. Wells St., Theater on the Second Floor
Best Of Annoyance Sketch
Jun21
Music & Comedy, Theatre & Performing Arts

Best Of Annoyance Sketch

Enjoy the best sketch comedy Chicago has to offer! The Annoyance Theatre has been at the crux of the comedy scene in Chicago for over…

Saturday, June 21st
9:30 p.m.10:30 p.m.
The Annoyance Theatre
851 W. Belmont Ave.
Al Jackson at The Comedy Bar
Jun21
Music & Comedy

Al Jackson at The Comedy Bar

Al Jackson is a Los Angeles-based stand-up comedian, writer, and TV/radio personality best known for his special “Comedy Central Presents: Al Jackson” and for his role…

Saturday, June 21st
9:30 p.m.11:00 p.m.
The Comedy Bar
500 N. LaSalle St.
LET’S PLAY A GAME: Chicago’s scariest short-form show
Jun21
Music & Comedy, Theatre & Performing Arts

LET’S PLAY A GAME: Chicago’s scariest short-form show

Who’s Line is it Anyways meets Fear Factor in LETS PLAY A GAME, a new short form show that’s a unique blend of comedy, chaos,…

Saturday, June 21st
10:00 p.m.11:00 p.m.
Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.
Teatro Zinzanni
Jun22
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Sunday, June 22nd
5:00 a.m.9:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Monday Night Concert Series
Jun23
Music & Comedy, Tours & Attractions

Monday Night Concert Series

Chase Away your Monday Blues with a Symphony of Soul! We’ll help you chase your “Monday blues”, aboard the 148-foot Tall Ship Windy as you…

Monday, June 23rd
7:00 p.m.9:00 p.m.
Navy Pier 600 East Grand Avenue Chicago, IL
600 East Grand Avenue
Tuesday Good Show
Jun24
Music & Comedy

Tuesday Good Show

Showcasing some of the best performers in the city, Tuesday Good Show is a free weekly variety show hosted by Nick Bonsignore and Keller Paulson.…

Tuesday, June 24th
7:00 p.m.8:30 p.m.
The Gallery Cabaret
2020 N Oakley Ave
Comic Court: The Best Comedy Show in the World
Jun24
Music & Comedy, Theatre & Performing Arts

Comic Court: The Best Comedy Show in the World

Would you rather be able to fly or be able to turn invisible? Who are we more tired of: Ryan Reynolds or Dwayne Johnson? Would…

Tuesday, June 24th
9:00 p.m.10:30 p.m.
The Lincoln Lodge
2040 North Milwaukee Avenue
Daniel Tosh Live!
Jun25
Music & Comedy

Daniel Tosh Live!

Daniel Tosh will come to The Chicago Theatre on June 25. Daniel Tosh is a comedian, host, writer and producer. After graduating from the University…

Wednesday, June 25th
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Lil Baby – WHAM World Tour
Jun25
Music & Comedy

Lil Baby – WHAM World Tour

Lil Baby is bringing his WHAM World Tour to the United Center on June 25! Joining Lil Baby will be special guest BigXthaPlug, NLE Choppa,…

Wednesday, June 25th
7:00 p.m.10:00 p.m.
United Center
1901 W Madison St.
Hooch & Holler Comedy Show
Jun25
Music & Comedy, Theatre & Performing Arts

Hooch & Holler Comedy Show

Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…

Wednesday, June 25th
9:00 p.m.11:00 p.m.
Bordel Cocktail & Cabaret
1721 W Division
Teatro Zinzanni
Jun26
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Thursday, June 26th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
Daniel Tosh Live
Jun26
Music & Comedy

Daniel Tosh Live

Daniel Tosh will come to The Chicago Theatre on June 26. Daniel Tosh is a comedian, host, writer and producer. After graduating from the University…

Thursday, June 26th
7:00 p.m.9:00 p.m.
The Chicago Theatre
175 N. State
Duluth: An Improvised Midwest Murder
Jun26
Music & Comedy, Theatre & Performing Arts

Duluth: An Improvised Midwest Murder

Inspired by the hit FX show “Fargo”, Duluth takes audiences into the world of true crime in the Midwest. Each week, the cast of Duluth will…

Thursday, June 26th
7:30 p.m.8:30 p.m.
iO Theater
1501 N. Kingsbury St.
Stray Kids World Tour [dominATE CHICAGO]
Jun26
Music & Comedy

Stray Kids World Tour [dominATE CHICAGO]

Stray Kids will make their debut at Wrigley Field in 2025! The performance at the Friendly Confines is part of the Stray Kids World Tour…

Thursday, June 26th
7:30 p.m.10:30 p.m.
Wrigley Field
1060 West Addison Street
Improvsed DCOM
Jun26
Music & Comedy, Theatre & Performing Arts

Improvsed DCOM

Dive into the nostalgia of Disney Channel Original Movies with the cast of Improvised DCOM! This All Star cast is bringing screen to stage every…

Thursday, June 26th
8:00 p.m.9:00 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Teatro Zinzanni
Jun27
Music & Comedy, Theatre & Performing Arts

Teatro Zinzanni

Tickets are on sale Now at https://zinzanni.com/chicago/ for Love, Chaos, & Dinner ! Teatro Zinzanni returns to the vibrant Chicago Loop inside the velvet walls…

Friday, June 27th
6:00 p.m.10:00 p.m.
Spiegeltent – Cambria Hotel
32 W. Randolph
The Infinite Wrench
Jun27
Music & Comedy, Theatre & Performing Arts

The Infinite Wrench

Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…

Friday, June 27th
7:00 p.m.8:00 p.m.
The Neo-Futurist Theater
5153 N. Ashland Ave.
ComedySportz Chicago
Jun27
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, June 27th
7:00 p.m.8:30 p.m.
Malarkey Comedy
1501 N. Kingsbury St.
ComedySportz Chicago
Jun27
Music & Comedy, Theatre & Performing Arts

ComedySportz Chicago

Chicago’s longest running and best interactive improv comedy experience. ComedySportz is comedy played as a sport, not comedy ABOUT sports (whew). Refs, fouls, points, games…

Friday, June 27th
7:00 p.m.8:30 p.m.
Malarkey Comedy Company
1501 N Kingsbury St
Chris Stapleton: All-American Road Show
Jun27
Music & Comedy

Chris Stapleton: All-American Road Show

Chris Stapleton is set to continue his “All-American Road Show” tour with a newly announced performance at the Credit Union 1 Amphitheatre in Tinley Park,…

Friday, June 27th
7:00 p.m.10:00 p.m.
Credit Union 1 Amphitheatre
19100 Ridgeland Ave
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